Gossip Girl: Jenny's Story
by WRitesALOt
Summary: Ever wondered what Jenny Humphrey from Gossip Girl does at Design School? Here is my own version of her life and the encounters she has with others along the way. Reviews are welcome! I'd love your suggestions and the author of the suggestion will receive a shoutout whenever the suggestion has been made.
1. Lights, Camera, Action- Reviews Welcome!

"I have no idea where they are, but you better find them."

Jenny Humphrey was one agitated woman. On her first group design project someone had lost her sketches and if they weren't found soon, they would receive a failing grade on their project. But it did help that the guy she was working with was sort of cute, for a dumb guy at least.

"_What is his name_?" Jenny thought.

Oh well. It didn't matter. She would be finished with this project whether she failed it or not. Her thoughts turned back home; to her brother and his fake relationship with the gorgeous Serena. All of a sudden, she heard a male clear his throat.

"I've got the sketches in my dorm. I just had my roommate check for them."

Ok. So maybe Eric wasn't as stupid as she thought.

"Jenny?"

"Oh. Right. Well lead the way. I don't have forever.

Eric just chuckled and began to walk out of the coffee house they were working in. He hadn't even been nice enough to offer to buy her a cup of coffee so she could pretend to turn it down until he insisted she just had to have it. She could tell that behind the cute face, there was nothing but air… and maybe a nice body. He looked like someone she had the biggest crush on back in New York.

"Hey Eric. Do you know a guy named Nate Archibald?"

"Of course I do. He's my cousin. Everybody around here knows that."

Silently, Jenny smiled to herself. She couldn't have Nate. No. That was impossible because Blair had basically kicked her out New York City and every place that wasn't Brooklyn. After proving that there was nothing for her in the city (based on a recent visit home) she decided she would settle for a quiet country life. However, the country life was everything but quiet. With all of the parties and mini fashion shows, Jenny found herself busier than ever. She liked her life away from the thrill of the Upper East Side. And she found that she was starting to like Eric more and more.

"Well, here we are. I'm sorry the room is a little messy. I swear your sketches are still OK."

Suddenly, Jenny found herself uninterested in the sketches strewn about Eric's desk.

"It's OK. Do me a favor? Let's not talk about this stupid project anymore. I think I can find us better things to do."

"But Jenny! The project is due first thing in the morning and I thought you wanted to finish this now?"

"That was before I realized how hot you were."

"Are you sure this is something you want to do?"

Before Eric had a chance to complete his sentence, Jenny was laying naked in Eric's bed. She settled in and waited for Eric to work his magic on her, but was getting agitated quickly. It took him way too long to put on a condom. He needed to move faster than that for her. She quickly pulled him on top of her. She wanted to hurry and finish this before her boyfriend Matt went looking for her.

Right before Eric entered her, someone came strolling into the room. It appeared to be Eric's roommate Josh. Jenny at this point was past the point of embarrassment. She quietly invited Josh to join them. While Eric made use of his time with useless foreplay, Josh quietly entered her, causing Jenny to cry out in pleasure. All of a sudden, she saw a flash out of the corner of her eye. Eric and Josh had set up a camera in their bedroom.


	2. Too Bad Jenny Hadn't TRIPPed Sooner

I know. I know. You wanna know who I am, however, it's not time for that yet. I'm still following Little Jenny Humphrey. When I'm done, I'll introduce myself.

Jenny needed to make a decision and she needed to make it fast.

She could either pose for the camera, or stop the whole thing altogether and destroy the tape. Ever since Blair destroyed her and kicked her to this small design school in New Jersey, she'd been keeping a low profile. She needed to bump her popularity status to the top of the charts if she ever expected to see the upper east side again.

"You guys are idiots for trying to hide a camera. Turn the damn thing off."

Eric got up and did as he was told.

"Here's the plan. We're gonna make this 'movie', but if we make it, it's gotta be good. Here's the plan. I want the both of you to make me the star of your little film. Do that, and I'll make sure that you get what you want in the end. Turn the camera on and let's try this again."

Josh got up and did as he was told.

Jenny performed like a true star, stopping to pose in front of the camera when she did something particularly scandalous with Josh or Eric, and after the video was finished, she uploaded it to me. This is what I realeased;

**Little Jenny Humphrey is an actress now. This isn't the sort of movie I'd ever watch or make. Let's see if Blair Waldorf is watching.**

"Now listen to me carefully. If anyone asks, it was my idea to make this movie. It was nice doing business boys."

With that, Jenny left the room, kissing Eric and Josh on the cheek and reveling in her newfound stardom. Project be damned, if she wasn't getting a great grade in Sketch Design, she'd get a wonderful rating in scandal. As Jenny walked to her door, she realized that she had just screwed Nate Archibald's cousin. Removing the key to her dorm from her purse, Jenny crashed into someone she couldn't quite see.

"Hey you idiot, watch where you're—"

Tripp Vanderbilt was standing before her.


	3. Vanderbilt Dogs Carry Expensive Fleas

"Ok, look. I think you've got the wrong blonde. If you're looking for your side piece Serena, she's still on the Upper East Side."

Jenny clearly was shocked to see him standing there. The last she'd heard of him was when him and Serena got into that car accident and he'd left her. The last I'd heard of him was when his wife threatened to leave him. Everything was about politics with him. Tripp Vanderbilt and Little J were a match made in hell.

"No. I'm looking for you. I divorced my wife Marlene and I'm looking to expose Blair Waldorf and win Serena back."

Jenny was all for exposing Blair, but there was one problem with his plan. Serena was 'dating' her brother and if there was one thing Jenny knew, she had to go along with Dan's story if she wanted to stay loyal to her brother.

"Look, I don't know who sent you here, but I can't help. I don't do scandal and facing off against Blair Waldorf is a trap no one should set for themselves."

"Nelly Yuki sent me. She knows you didn't really sleep with Chuck Bass and she says she's a source for you."

That bitch Nelly. She could never keep a secret. Jenny knew she was in too deep to turn back now. If she decided not to help Tripp, Blair would turn on her, and clearly that was the last thing anyone needed.

"Fine. I'll help. Help. You'll have to break Serena and my brother up, and everyone knows a Blair Waldorf sabotage is extremely difficult. I don't even have social standing anymore."

"I'd call this video all the social standing you'd ever need."

My GG blast had gone viral, showing all of Little J's goodies to the world.

"I don't have a hotel room or anything, and I'd like to get started right away. Is it cool if I camp out on your couch?"

"Well congressman, I don't mind if you do, but once you cross the threshold, you do what I say."

"That's what I thought you would tell me. I know what and who I'm doing."

"I hope so Tripp. I hope so."

So little J has backbone after. I shudder in delight of the thought of her ruining Waldorf. I wonder if B will even see it coming.


	4. Double Crossed by B?

Jenny needed to make Blair notice. She had shunned her, and now it was her time to pay. B was under the impression that Little J had slept with Chuck Bass. If I was Little J, I would have done more than make an impression.

"Tripp, get up! You're crushing me!"

Trip rolled over, taking the pillow and blanket with him.

"Vanderbilt! I didn't start sleeping with you to freeze my ass off. GIve me the blanket back!"

The minute Tripp showed up at her door, Little J knew she'd sleep with him. I knew she'd sleep with him the moment I heard he left the Upper East Side looking for her.

"Sorry babe. I didn't realize. I must say, I like you better without the blanket."

Babe. Jenny wasn't having that. Pet names meant attachment. Attachment wasn't something Little J was hoping for.

"Tripp, we have to work on this plot. Time to sabotage Blair Waldorf is running short and you being here is starting to wear my patience thin. Besides, she leaves for Monacco Thursday with that prince she supposedly loves. If we don't get her now, we won't get her at all."

"So what are you suggesting babe?"

"I'm suggesting you stop calling me babe. I'm requiring us to get off our asses and actually do some work. I'm demanding you go get me coffee. I'm wishing for a few more hours of uninterrupted sleep."

"Fine. I'll go out and get coffee. You shower and get dressed and we'll start planning. I love you."

"I love you too."

Little J was lying. She did it well. Tripp was lying. Unbeknownst to Little J, he did it better.

Outside, Tripp removed his cell phone. I watched him. I took a picture of it and added it to my gallery. I wanted him to get caught. I just needed to know how and when to use the photo.

"Yes Blair. I know you've been calling. Yes Blair. She's completely enamored with me. It'll go as planned. I'm not scared of Jenny Humphrey. I'm a congressman for Christ's sake! No. She doesn't know anything. She still thinks you're the target. Ok. Yes. Give Charles and Nathaniel my best."

The worst thing I have ever done in my life is miss that conversation. I watched him hang up the phone, and head to the local coffee house to fulfill Little J's demands. I was starting to wonder. Who was scamming who?

This could be the scandal to end all scandals. I'd catch it all. Little did they know everyone would pay for their crimes soon enough.

You know you love me,

XOXO

GG


	5. Bye Bye Little Baby Bass

As she put on her make-up, Jenny contemplated the last few guys she'd slept with. Eric, Josh, and now Tripp Vanderbilt. Nathanial Archibald had ruined it for everyone. SHe'd fallen in love with him against her better judgment and he had spurned her because she was too young. Now, she thought about it, and she liked her running total of Vanderbilt men she'd screwed. As she finished the final touches of her lip gloss Tripp walked in the door.

"I've got your coffee honey. Now that we have something to refresh us, maybe we can go for round two?"

"Tripp, we have to get down to the plan."

"Ok. Ok. So what do you wanna do?"

"Clearly, there's nothing Blair loves more than a good dose of Chuck Bass. The plan shouldn't be to detroy her. Why not kill two birds with one stone? Destroying Chuck hurts Blair enough so that she'll be hurt too."

"Brilliant baby. Now, how do you plan to accomplish this?"

"Ok. Before we go any further, let's get one thing clear. This 'thing' we have is nothing but a business arrangement. Sure, we're sleeping together, but other than that, all we do is plot. I'm not your baby or anything else. We are not getting together."

"J, you sound like a Taylor Swift song. Maybe we won't be together now, but as soon as we've accomplished our goal, I'll marry you. I'm sure you'd look great on my arm in Washington, D.C."

Little J smiled to herself.

After she was done with him, he'd be lucky if he ever held an office again.

"Ok 'honey'. I've got a class right now. We can talk about this plan later."

"See you later."

Now the picture I took proved Little J was a liar. Instead of showing up for her intro to fashion marketing class, she went to go meet someone.

She was running late.

Nate Archibald hated to be kept waiting.

She spied him sitting in the same coffee shop Tripp had visited minutes before.

"I asked you to destroy my cousin, not sleep with him."

"What's the matter Nate? Are you upset because him and I are a better fit? I got what you wanted. He's eating out of the palm of my hand. Now, all I have to do is switch gears. He's under the misgivings that we'll be together one day. I want all of you out of my life, and I want you out for good. You owe me half of the money now. I'll take the rest after the job is done."

"Relax. I brought your money. This better work Jenny. Seriously. If I have to clean up after you there will be a serious problem. The amount of trouble you'll be in is unspeakable."

"What's the matter Natey-pooh? Are you gonna spank me?"

"Stop fooling around and tell me what this plan is."

"Oh, I can tell you now. The plan is simple. The baby Blair is carrying? Let's just say she won't be carrying it for long."

So Little J does have a dark side. The moment my cameras pick something up the better. Ah. Decisions, decisions. Should I save the Little B, or watch her die like Little J's social standing?

Regardless, you know you love me,

XOXO

GG


	6. Til Death Do Us Part

"Tripp honey, are you all packed up and ready to go? The train leaves in an hour and I wanna find a nice window seat."

Today would be the day Jenny would put the first part of her plan into action. Riding the train into New York with Tripp, Jenny would do some shopping hoping to be photographed by yours truly. Usually, I'd have my sources following her, but for the scheme to end all schemes, I figured I'd do the groundwork myself. Little J was all ready to go, but you should never underestimate a Vanderbilt man.

"Jenny sweetie, I can't find our train tickets."

Jenny spun and even the spit flying from her mouth had heat.

"So help me god, if you lost those tickets, you'll be sleeping outside for the rest of the planning."

"I said I can't find them. Wouldn't that imply that they're already lost?"

Jenny sat on the bed in a cloud of anger. Someway, somehow, she'd have to call Nate and notify him of the change of plans. There was one thing that was clear. Nate was definitely the brightest Vanderbilt Man.

"Thanks a lot Tripp. There's no way we can make it in the city in time for me to do my holiday shopping."

"J baby, Christmas isn't for another two weeks. I'm sure we can go another day."

"Tripp. You don't understand. It needed to be today. I needed to go shopping today."

"Why today Jenny? Was there something special that was to take place?"

"There was a sale."

"A sale?"

"Yes. There was a sale at Gucci and I needed a few purses."

"You must not shop at Gucci often Jenny. Tell me the truth."

"What are talking about Tripp?"

"Women who frequently shop at Gucci call them bags, not purses. I'm not messing around Jenny. Tell me the truth."

Little J had been caught in her big lie. I watched her as she stammered for a new, better lie with less holes.

"Ok. Tripp, you want the truth? Let's talk. I wanted to stop at Tiffany's."

"Tiffany's?"

"Yes. I put a promise ring on hold for you for Christmas and I wanted to pick it up while you were handling business. I figured that if I got it while you were out and about, I'd need no explanation for going there and I could surprise you when I gave it to you when we got home."

Tripp slumped onto the bed. Surprised by Little J's sudden act of kindness, a slow smile spread across his face.

"The good news is, I'd have loved your surprise and there is still time for you to give me the ring. We'll go another day. It'll still be just as special then."

I watched as Little J forced a smile. There was no way she wouldn't destroy Tripp Vanderbilt. No matter how cute he was, she would take him down.

"Excuse me honey. I need a minute to emotionally gather myself."

Rushing to the nearest open door, Jenny rushed to call Nate. She ended up in my dorm. Yes, I'd camped out in fashion school.

A girl loves to be comfortable.

If you love to hate me, don't you really love me anyway?,

XOXO

GG


	7. Mommy Dearest

"There's no way you're gossip girl. I refuse to believe it. Why would you sit back and let all of this happen?"

Revealing myself to little J hadn't exactly been what I had in mind, but it would do. After all, she had stumbled into my dorm.

"And seriously? Professor Green? Out of every single one of them you had to screw the one I liked?"

Yes. It was true. David Green was in my bed after all, but why was that any of her business.

"Look Little J. I know what you're doing, and I'm here to merely observe and offer my services."

"Services? Oh no. Absolutely not. I know exactly what happens when you offer your services. Do you honestly think Nate Archibald would continue to fund me if he had any idea I'd even talked to you? He hates your guts. After the Blair running me out of town thing, I can say I'm not in your corner either."

"Listen Little J. I can help you. You name it, I can do it. I know you're playing everyone. There isn't a thing you've done that I haven't seen. So how about we do things my way. Prof. Green is going to excuse himself back to his study, you're going to call Archibald on the phone, and you're going to tell him you've run in to me. The minute you think you can get over on me, I tell Tripp your little plan and the game will be all over. Mark my words Little J. I'm here for the long haul."

I turned around then, assuming she'd do as I said. Who would've thought the little bitch was going to try and run? I caught her by her hair. I had screwed things up when I'd tried to make Serena my ally. I would not lose another minion to foolish thoughts about shutting me down.

"It won't work. I'm your new best friend until this thing is over with and after, whenever I ask something of you, I'm going to expect a reply. You can't play me J. I created the game in the first place.

I let her go. She picked up the phone and began to dial.

"As a matter of fact, you won't tell him you've seen me, you won't tell him you've heard I was here. You'll tell him you've met a new friend named Anastasia and she has a lot of contacts that can help you."

Why was I feeling Russian all of a sudden?

"And when he asks where you know me from, tell him I'm an old friend of his father. That way, he'll think he can trust me. Oh, and one more thing Little J."

"What else could you possibly want from me?"

'If you tell my daughter about this, I'll end you. Again."

**A/N: Hopefully you guys liked this chapter! Oh the suspense. Will we find out Gossip Girl's identity after all? Please, Please, Please review this and make suggestions. Your suggestions and reviews are always quick encouragement to write more.**


	8. Trouble At Home?

"Look Archibald. You didn't see her or hear her. If she finds out I've told you who she is, I'm over. This, is over. Everything we would have spent our lives doing for the past few years would go to waste. The millions of dollars you've put into this plan will go to waste and I know you of all people don't want that to happen. Pretend to cooperate please! Blair and Serena can't know who she is. They just can't! There will be a whole mess of stuff to happen. You just can't tell!"

Looking out of my dorm room window, I could see Little J on the phone with Archibald. I knew the little bitch would betray me the minute I showed her who I was. I also knew that she would try and betray me. It was fine. I played the game of blackmail better than anyone, and I'd dare Little J to try and show me otherwise.

"Look. I don't know what you expect me to do about it. I'm supposed to practically be her slave. Clearly this isn't something I'm happy about, but it has to be done. I'm not dealing with it anymore. You want to get rid of her? Call your grandfather and ask for some help. Clearly Bart Bass can no longer be one of our resources. Why'd you have to go and cook the books?"

The panic on her face was almost comical to me. There was nothing she could say or do to get out of this one unscathed. Either I or Vanderbilt would take her down. I hoped it would be. Vanderbilt has such a pretty face. Why waste it?

"I've gotta go. It looks like it's time to call in all of your favors. Yes. That includes your grandfather and Diane and the Captain. I have no more time to talk to you. I'm pretty sure she's watching me through the window. Bye. Whatever. Keep your clothes on until I get there."

"Come here. I hate that phone Little J. Here's a new one, and if I ever find out you've seen another gossip girl blast, you're over."

I wanted to make sure I could manipulate J's little world without her even knowing it. What better way to do that than to block her out of her favorite gossip site? I planned on fully controlling her and there was nothing anyone could do about it. I'm all-powerful, all-knowing. Second only to what some people say must be god. At the end of the day, who on this coast could possibly shut me down?

I knew one thing she didn't know. Rufus Humphrey had gotten married, giving Little J a new mommy. And as I blasted out to the entire world,

_Mommy's having a baby, Daddy's already crazy. Brother's officially homeless and Little J will soon be joining them._

_You know you love me._

_XOXO,_

_Gossip Girl_


End file.
